I spent yesterday morning — a weekday, a Thursday — sitting on a chair outside a cafe enjoying the last bits of warm weather in New England, just reading and doing a bit of people-watching. Toward the end of the three or so hours of blissful me-time, I realized something startling.

I’ve become that guy.

You know who I’m talking about. Don’t pretend you don’t.

I’m referring to the guy you occasionally see at your local coffee shop at eleven in the morning with flip-flops on — the one who seems like he doesn’t have a care in the world.

You wonder what’s going on there. Can’t help yourself. Because he’s definitely not working. You can tell since he’s reading trivial fiction, maybe Girl with the Dragon Tattoo or Snow Crash or Clifford The Big Red Dog, and there’s no laptop to be found anywhere.

He doesn’t check his phone. You wonder if he even has one.

You might see that guy jogging down local streets at eight thirty in the morning while you’re commuting to work. Eight bleeping thirty! If he had a standard 9-5 job — if he worked in an office — he couldn’t be jogging, because he’d have to be in a car or on public transit, just like you.

But he’s not. And you notice that guy exercises without even putting headphones in his ears — without even music to distract him from his life, the way most people seem to need. He even has the nerve to smile.

I mean, who the hell smiles while they run?

It’s that guy.

Sometimes you see the same son of a bitch at three o’clock and he’s just meandering down the sidewalk, without kids or anything so you know he’s not a stay at home Dad. It doesn’t appear that he’s doing anything at at all — he’s impossible to figure out.

You might see him when you’re on a short break from work and you’re driving down the street to run an errand before frantically returning to the office so you can check email and respond to people in a timely manner and, so you can synergize and continue to collaborate and get some face time in before you move projects forward. If you make it back quick enough, no one will suspect you were gone. After all, if they did, they might question your commitment to The Company.

But that guy doesn’t appear to have any company of his own to hurry back to. That guy doesn’t appear to be liaising with anyone. That guy isn’t even wearing office-appropriate clothes — he’s got a goddamned Super Mario Brothers T-Shirt on.

You wonder what his story is. He’s in his mid or late thirties — Far too young to be loaded or retired, but far too old to be living with his parents. He must be able to take care of himself without a job. What’s the freaking deal, there, anyway?

And why does he look so. motherloving. relaxed (!?)

You have your own ideas. Maybe he’s a bum. Or he’s one of those lucky trust fund kids. It’s possible that guy is a lottery winner — hey, someone must be winning those things. There’s also the possibility that he’s laid off and just working through a temporary unemployment gap.

Consider the possibility, though, that none of those suspicions are true. Because they certainly don’t have to be.

I should know. Like I said, much to my surprise, I’ve become that guy now — and I did it by working an unspecial IT/software job, saving a lot of money, and living a normal life. I did it by spending consciously over a decade and a half, instead of reflexively opening my wallet for every trivial want that entered my brain. I did it by learning how to invest in the easiest, laziest, and yet most successful way possible: Shoving a high percentage of my earnings into index funds and waiting for the stash to compound over a bunch of years.

I did it by achieving financial independence. Anyone with a decent paying job can do the same without too much trouble.

Yeah, it’s funny the prejudices people have against the way people dress. Seems like most assume that if you’re not looking super trendy that you must be poor (the so-called bum you’re talking about.) Hardly anyone seems to think “That person is smart for not spending a truckload of dough on clothing.” But people around this part of the internet do, at least — Awesome.

My mom used to love telling the story of a bum everyone used to see walking around Key West. He wore the most bedraggled torn shirt & cutoff jeans, didn’t shave, was seen drinking in the morning, and rarely had a care in the world. That man was Ernest Hemingway. One story goes that Hemingway met Joe Russell, his fishing buddy, when Russell cashed a royalty check that the local bank had refused.

Judge people by their appearance and you’ll likely miss out on knowing the most interesting people in our society.

I don’t go out enough to become that gal, and I may be a bit too old, and our society better accepts unemployed females – but yeah, I am that gal. Walking the dogs at 9 or 10 am (though the little bastards won’t let this be a leisurely saunter), going to the grocery store midday, wearing she ports and flip flops every day….

My wife’s she port didn’t work at all and we had to bring them back to the “all ports for him and her” store. Turns out they only work once you are FI, so every potential buyer should be made aware of that.

I have to confess that, until discovering MMM and starting the FI journey a little over a year ago, I definitely assumed the worst about “that guy.” At best they started a business and ‘got lucky,’ and at worst they were a trust fund baby. Under no circumstances could I accept that it was my fault that I was in my car commuting instead of being out there with ‘that guy.’

I’ve probably got a decade and a change until I get to be that guy…and I can’t wait.

Just got back from a coffee shop with my dog and this was basically me…for 30 minutes while on my lunch break. It felt nice; to disengage from the world for a few minutes, enjoy a coffee, and a pastry is just a taste. Back to the race

Heck yeah dude! I’m that guy too. We just spent the morning bumming around a state park. Smiling, finding spiders with our 3 year old. Laying on rocks in the middle of the river. Enjoying the fact that almost everyone else is at work while we’re out enjoying a beautiful fall day in a nearly empty state park.

Sometimes That Guy is in disguise. Did I just see That Guy raking leaves at 10 am on a Tuesday morning? Or is that just a normal person getting paid to keep up a working professional’s lawn? Dog owner or dog walker? Hardcore leisure cyclist or bicycle messenger?

Her experience is different from mine so far, mostly because I was so busy with our physical relocation (we moved..)

Right now she’s in the ‘rest’ phase, sleeping a little later than usual, reading. She brought an old tea-set out and makes a pot of black to drink while working through books on the couch. She gets out of the house every day to a) spend a couple of hours with her sister and nephews after the school-day is over and b) go for a long walk with me. But mostly she’s just relaxing and absorbing the lay of the land, which is very different than anything she’s previously been exposed to.

A very serious post, quite unlike some of your previous ones. Nonetheless, I enjoyed it tremendously.

I often get stares from old-age retirees when they see me in the public swimming pool on weekday mornings for consecutive weeks. I wonder if they think I am a trust fund kid/lottery winner/tech entrepreneur/unemployed. Maybe, just maybe, I will chat them up soon. ;p

Just curious, as you approach half a year of retirement, are there any “downsides” to it? Would be great to hear it from you personally. Or is it a blog post in the pipeline?

>>Just curious, as you approach half a year of retirement, are there any “downsides” to it?

There’s an adjustment for everyone. It’s a personal experience, unique to the individual, because of the variables that go into it — expectations for post-work life, energy levels, state of burnout from previous job (high? low? Nonexistent?), other commitments in life, relationship status, personality type.

Some of the adjustment is challenging, which I suppose you *could* list as negative. I do not. I view the adjustment phase as interesting, reflective, and exploratory. I do have a post I’m working on which details certain aspects of this phase that I didn’t cover yet, but man is it long and, at times, very weird, personal, and judgmental. If I can get it into a state where it feels right, I’ll publish it.

I’m an old guy, 65 yo, but I’m joining the retiree ranks in 50 days exactly. Wish I had figured this stuff out decades ago, but as little as 5 years ago, I had a mortgage, home equity loan, car payment and credit card payment. Started working hard on these, then found MMM about 4 years ago, and worked harder. All the debt is dead and buried, I have about $75,000 in savings and about $300,000 in IRA/401K which I really will never need to touch thanks to social security and a small pension. I don’t go to coffee shops now (MMM frugal habit) but I might do this a couple of times a month after retirement, just to enjoy sitting somewhere, leisurely, during the work day. Also I can’t wait to increase my daily 30 minute workouts to more like 45 minutes a day. And travel! Wow, I get to take leisurely exploration trips and never have to rush, can dilly dally and see the sights. I’m so excited to get started I can’t see much need for decompression time – I’ll just glide into the next phase of my life.

Yes, she did (finally) pull the trigger after finishing a final project at work. They did all of the usual to try to keep her but when you’re mind is made up, that’s that. Unofficially, the door’s open for her to return though.

I wouldn’t say she was against it so much as she had mixed feelings and legitimate concerns — for example, she definitely needed convincing that financially it was going to be O.K. There’s also no doubt that being a part of my own quit-work-and-decompress experience had an impact, too. She says I act happier, which is no surprise, considering I absolutely am. And then there’s the fact that I’m actually able to do the more important things in life now, to spend more time with family, to visit old friends, and on and on, and she wanted to do the same.

Although it does appear that #1 on her agenda right now isn’t family but rather watching every single Poirot movie ever made. 😉

I find this very encouraging, as I would really like to retire (maybe with a part-time gig) in the next 5 years. At that point my daughter will just be starting school, so not needing full time child care any more, meaning I can spent lots of time with her but also have some time to myself each day to be “That Gal”! I already have a long list of retirement projects that I want to embark on in those hours – including loafing around in coffee shops (but also some more creative endeavours!)

However, like your wife my OH is much less keen (perfectly happy for me to do it, but less keen to have it for himself!) I think his reasons are a bit different: he has a bit of a protestant work ethic so there is a bit of guilt, and also a real sense that there are still things he wants to “achieve” at work, and that he is just not ready to retire yet. But by the time I retire we’ll both be 45 and I suspect that will feel a lot more like “time” to him (he works in finance where people don’t tend to hang on into their 50s anyway).

For myself I do wonder/worry a bit whether I’ll miss some of the better aspects of working life (I’m a consultant and it’s actually pretty nice to be consulted on things and know stuff and have people care what you have to say). On the other hand in terms of how I actually spend my time 90% of it is really grind, and often pretty stressful time-pressured grind, which is totally bearable but by no means fun or exciting. I am a natural optimist, and I believe I can do better than that in my retired life!

Your story is very encouraging in that regard, so thank you for sharing.

Same thing happened to me. I went from an irritable woman to an easy-going, happy person. Now, I’m that woman at Starbucks who stays for 2-3hrs and might be playing on laptop or reading a book. Productive in my chosen pursuits and pleased as pie that it’s because I want to, not because I need to.

Great post! I want to be that guy! Unfortunately, I don’t have an unspecial (but, I assume, well-paying) IT/software job in the U.S., so it’s going to take me a bit longer. But I hope I’ll get there one day. I have to.

Just wanted to say thank you for keeping your blog going. I check for updates about every day even though I know new posts only happen once a month or so. You have a very unique perspective that I enjoy. I’m working to be “that guy” as soon as possible.

That’s definitely the goal! Only worry about what you want to worry about and obtain the freedom to do what you wish with your time – whether that’s leisure or seek out other opportunities. I do see THAT GUY and you really can’t help but wonder how he got there . . . but now I wonder how he got there not in a jealous sense, but out of curiosity. Maybe you could learn a thing or two from That Guy. Nice write up!

Wow, going to tell my 6 year old that Clifford the Big Red Dog is trivial fiction. How dare you! Nice write up. I just assume that guy is in between jobs, living in mom’s basement, or a spy. I like to think spy at the end of the day. One day he’ll just disappear, off on a mission across the world or killed in action….but really his mom just made him get a job.

My neighbor for years always had the light on at 2am. It drove me crazy so I finally asked and he said he just wants to make guitars in his basement and quit his I.T. job. Save and do whatever you want, its awesome. Just know that everyone is always staring at you and wondering….freak.

Combine it all and he’s a guitar-making spy working an IT job remotely from his mother’s basement, gathering intel on corporate internals and sending them to North Korea so they can make another dramatic security breach, Sony-2014-style. Problem is that now he’s got this big red dog, and well, it’s hard to keep a low profile and do the whole espionage thing effectively when you’re taking care of Clifford, who is pretty conspicuous if I remember correctly.

I had a “that guy” feeling when I went to the bank earlier this week. I was inquiring about one of their financial products and, upon answering all their “assets – liabilities” questions, I officially got the “you’re one of the weird ones” looks. PRICELESS! 🙂

Cool comment — I’ve had something similar to that feeling when working through a financial evaluation with a guy from Fidelity last year. Like: How did you manage to accumulate a great stash at your age? It seems like the very last guess most people make is “working a pretty regular job and saving a lot…” It’s the least weird option, actually — statistically I’m sure it’s the most likely when compared to lightning-bolt events like inheritance and winning at the dog track — and yet it remains out of the comprehension of your average person.
And when you explain it this way, the person asking the question is always, in my experience, profoundly disappointed that the solution is so simple (and seems to require discipline and persistence — traits which are Known to Suck.)

>> I officially got the “you’re one of the weird ones” looks.

You’re hardly weird around these parts — love hearing from people who are careful with their earnings and using that money to generate increased options in life.
Nice!

I get this every time I call my 401(k) provider. It drives me crazy! Why is it so abnormal to have over $100k in my 401(k) in my late twenties?! All I did to get that balance was to max it out for five years straight, get some matching money and some growth.

I’m ‘that guy’ too! You describe beautifully what it takes to become ‘that guy,’ and it’s not rocket science or fabulous good luck, is it? Many friends and acquaintances are envious now and seem baffled how I was able to become ‘that guy.’ That the answer might lie in their ‘spend-every-penny-you-earn’ philosophy never, to my amazement, seems to dawn on them.

Loved this. Great writing! I’ve felt very… conspicuous, being That Gal. I’ve even felt a little guilty, though — as I enter month five of FIRE — I’m beginning to realize that that’s because I was brainwashed and primarily (not only, but primarily) conceived of myself as a “worker.” That’s just the other side of the “people as consumers” coin. I am finally beginning to enjoy being That Gal more and more, and posts like yours certainly help!

I’ve been that guy for a little over 3 years or so now. Everyone I know is envious to death of my FI, and those I newly meet all give me strange looks whenever I tell them I am retired and tell me I am too young to be retired hahaah. I am below 40 btw.

Beautiful!! I’ve worked in financial services all my life and one of the things I tell recent college graduates is to aim to be that guy. The guy who wears shorts and a t-shirt at 2:00 pm on a random Tuesday afternoon, that’s the type of guy you should aspire to be. Not worrying about putting up with cubicle crap and corporate non-sense… The sad thing is most of these young kids don’t listen and the first thing they do is get the fancy car, expensive apartment lease and the list goes on and on….

Loved this, especially as I am a kind of older, balder, Scottish version of That Guy! Happiness really is a Monday morning, 11am, a good cup of coffee in a nice cafe watching the world go by. I’d agree with another commenter though, who says it’s the Old Age Pensioners who I think wonder about me more when they see me. But perhaps it’s because, as you point out in another post, young people are TFB (Too Fucking Busy!) to notice. I spent about thirty years in the dark not knowing about the existence of That Guy because I was TFB. Until I read Jacob Fisker.

I enjoyed this post. I used to work in a part of town that was full of “those people”. Yoga pants, not a care in the world, and always at the mother loving coffee shop. I can’t imagine they’re all FI, but maybe. I’ve just started my journey into frugality and can’t wait to be “that girl” chilling in stretchy pants at noon some Tuesday in the future.

Great post, I can relate to so much of what you mention. Not only does this apply to people who have FIREd, but also to those living unconventional – and less work-centered – lifestyles. To me, it feels like being out of the Matrix, for better or for worse.

So many facets of society are governed by assumptions concerning work, money and time. Confronting these assumptions head on with a life decision such as yours has got to be challenging.

How do you deal with the relationships aspect of your “new” life? As a 24 y/o barely needing to work to keep myself going, my lifestyle contrasts sharply with other people, and this impacts what I actually enjoy doing socially. I mean, how can you be interested in 7 to 9’s, getting wasted on a Friday night or condensing travel into short periods, when you’re out of the worker lifestyle? Conventional social interactions are intimately motivated by a busy worker lifestyle, and now seem rather bland to me.

Have you found people who share a similar lifestyle, or are you juggling between friends based on their free time? (Which is what I basically do). I do have lots of projects and am rather introverted by nature, but something about having to wait for the week-end to see people bugs me. I feel like I broke out of jail, but left my friends inside.

You’ve hit on one of the main challenges of pursuing this lifestyle. People need people, but if you’re not working, it can be difficult to surround yourself with peers because there are so few of us previously professional humans (percentage-wise) that willingly and consciously execute plans to not work much, far ahead of standard retirement ages.

>> I mean, how can you be interested in 7 to 9’s, getting wasted on a Friday night or condensing travel into short periods, when you’re out of the worker lifestyle?

You can’t. Or, at least, I haven’t been able to. You no longer “need” to go get hammered on the weekends to celebrate being released from your job for a couple of days. Or get drunk to blow steam resulting from work stress. Or watch a sports game that you don’t even care about on a weekday night because you’re too tired to read a book or whatever. None of these things affect you any longer, so some of the activities that your average person enjoys will no longer be appealing to you. That’s just a fact.

>> Have you found people who share a similar lifestyle,

Not really. One of my goals in this whole journey was to not allow my life to revolve around the fact that I’ve retired early — I don’t want to only hang out with others who are on this path. (That’s probably also part of the reason why the blog is petering out… sorry about that.)

My reservation is that taking that approach might restrict my views into the human experience — I find it more interesting to hang out with people who don’t share my views. Not sure if that makes any sense — it does appear that most people doing the early retirement thing in a serious way wind up seeking out like-minded people specifically so they can hang out with others that think exactly like them. They essentially want to join a cult.

While I think this is fine, if that’s what you want, it’s not for me. I continue to value the friends in my life who do not think the way I do about finances.

>>something about having to wait for the week-end to see people bugs me. I feel like I broke out of jail, but left my friends inside.

This can change if you have a family — you can hang out with them during the week. I also don’t wait until weekends to ask friends if they can have dinner. Since I’m flexible, they can pick the day. I’m generally much more social than I was when I was working.

Still, there are also occasionally gaps where I don’t see people for the majority of a day, which still feels a little weird. If you’re working — even if you’re not socializing — chances are you’re around people.

This is one of the reasons why I still go to cafes once in a while — just to get out and people watch in a not-too-creepy, mostly-socially acceptable way. For $2, I can sit at a table for half a day, just reading or writing or messing around on the internet. Sometimes I’ll meet someone new and we’ll chat a bit. God, I met a dude from Oracle the other day who is in his early 60s and still working — he said he’s been grinding away ever since he finished his masters in his 20s. Smarter than me, no doubt, but I was surprised he still found it necessary to work. Must be making 150K minimum, perhaps 200K or more — my brain crunches the numbers on what he’s earned over his career and it staggers the mind. Why is he still working? I really hope he loves his job, but fact is he was complaining about it even during our brief conversation. I will probably have these types of thoughts for the remainder of my life, but I can hardly share them with him.